This post may contain affiliate links that help support my business in creating content like this. If you make a purchase using one of these links, I may receive compensation at no extra cost to you. Read my disclosure for more information.

With just a duffle bag and backpack in hand, I set off for what would be a week of all things new. Having never been sailing before, my expectations around what seven nights on board a 50 foot sail boat were limited. I knew the Aegean Sea for its crisp blue waters with turquoise coves. I had fond memories of Santorini and the caldera’s mesmerizing sunsets. 
I was ready to find out what life on board with G Adventures for their Santorini to Mykonos sail trip would be like.

Life at sea is different. It has this edge of being beautifully quiet. It could be boiled down to you, the water, and a horizon — yet there is so much more. You get to see things from a different perspective. You feel the wind in your face as the sun rises over a quiet port. You have access to exclusive bays and beaches only reachable by boat. And all the while, each island you arrive to awaits for exploration. 

As we winded through the Cyclades, we made ourselves homely in what was first an unhomely place. Life on board seemed to pick up a rhythm as all of us moved through the day. Each lending a hand, we did what we needed to do. On the deck we sat around the table laughing over games of cards while we sailed the long hauls, spotted dolphins, and even “increased the sheets.” 

When I think of the Greek way of life, sailing seems to by synonymous with the culture. Slow mornings, easy afternoons, and long dinners — all of which we did on board. Luckily, I got to go with my friend Jaharn of Mister Weekender for what was a week of adventurous memories, and smooth sailing. 

Here’s what to expect when sailing Santorini to Mykonos with G Adventures:

The Boat
First and foremost, it’s tight quarters. However, if you’re looking for an authentic sailing trip this is it definitely right up your alley. The boat is clean and your group on board (max 8 passengers + captain) helps maintain the cleanliness. There is a kitchen with sink, refrigerator, and stove top. The bathroom experience will take a while to get use to and your captain will go into great detail on how to use the toilets and shower. You will need to pump in water and pump it out into the tanks to use the toilets. And yes, there is warm showers! One thing to note is that electricity is limited to when you’re at port and when you do get a plug in. I often plugged in at cafes at night when we ate dinner to charge up — also a backup charger like this one or this one was a huge help on the boat. 
For sleeping, if you get a bunk room or the twin room, both are fitted for two people with a small bed, linens, fans, windows, and drawers. I found that keeping the space organized and cleaned made the tight quarters quite doable. Also packing minimally was an incredible help to space as well. Also note, there is a bit of rocking when you sleep, so I found that wearing these sea bands helped with seasickness. 

This is the part you’ve signed up for. Expect to be involved as much as you want or as a little as you want. I thoroughly enjoyed getting to learn how to do the knots, how to anchor, and prepping the boat for sailing. Our captain really gave us a great introduction to sailing, providing an opportunity to feel like we were a part of the logistics to making the trip happen. The boat also has a motor which comes into aid when the weather isn’t ideal for actual sailing. We had a few times where we got to “sail,” and when it happens, the experience is smooth and exciting. A few of the passengers even got to take the wheel and learn how to handle the boat whilst sailing! 

Food & Such
Once on board, everyone pitches into the “kitty” ($50 euros pp), and this is helps cover the costs of food and water for breakfasts and lunch. (There will most likely be money left over.) Every day we went shopping, grabbing food to make meals while at sea. Every dinner was at a port, and the best part is your captain knows the best local spots, so be prepared for incredible Greek food. 

As you come into port each day, there is a wide variety of experiences to be had. Your itinerary is completely dependent on the winds and where your captain feels it is best to go for the weather. This allows flexibility to time everything. Here’s where we what we experienced:

+ Fira: Arrived the first day, went and had a sunset dinner in Fira overlooking the caldera.
+ Manganra bay: On our way to Ios, we stopped in this beautiful bay to have a swim in the turquoise waters.
+ Ios: This adorable chora was incredible to explore by foot. 
+ Irakila: On our way to Naxos we made a stop to see the crystal clear waters and snorkel over the Italian World War 2 plane.
+ Naxos: Spending two nights on this island was great as we had an opportunity to explore the chora. The next day a few of us rented a car and explored the island. The island is rather large and getting to see its pristine beaches and the history at the Temple of Demeter made for an exciting experience.
+ Mykonos: Explored the old port, rented ATVs to see all the beaches, and relaxed by the beach.

(Click through for more photos…) 

Good to Know / Tips

+ Sailing is not for the faint of heart — the Aegean Sea can have seasonal heavy winds, meaning the boat will have its fair share of rocking. I felt safe the entire trip (even with my previous fears of the ocean) as we were in good hands with an experienced captain, even when we hit 45+ knots. 

+ I suggest to arrive a few days early for your trip in Santorini as it is such a great island and spend a few days in Mykonos or Athens afterwards to maximize time on ground.

+ Space is limited — you have to be comfortable with being in tight quarters with people you don’t know. Trust me, at the end of the trip you’ll all be friends and it’s great to experience it with new people from all of over the world. This was one of the highlights of the trip. 

+ Be sure to pack appropriately as night it can be cold, even when during the day you’ll be in swimwear.

+ Best time of year to go: June or July for the warmer weather.

+ Getting to travel with G Adventures gives you an opportunity to experience Greece like a local. Your captain always points you in the right direction when on an island to truly get off the beaten path, and has endless amounts of resources. Be sure to ask your captain for the best local knowledge!


Tempted to try a European Sailing Trip with G Adventures? Visit and receive 30% OFF select trips. 


*Bon Traveler was welcomed as a guest of G Adventures. As always, all opinions are own.

PS — Are You Booking a Trip Soon? Use My Booking Checklist!

These are the sites I use most to book my own trips. Using the links below is a great way to support Bon Traveler’s travel journalism at no extra cost to you. If you need help organizing your itinerary, get my free travel itinerary template here.

1. Book Your Flights

Use Skyscanner to find the best flights. It searches 100s of airlines and websites across the globe to ensure you’re not missing out on any route options or deals.

2. Book Your Accommodations

Use for hotels and guest houses. They have the biggest inventory and consistently offer the best rates.

3. Book Your Tours & Experiences

Use Viator or Get Your Guide to find the best tours and experiences. They are my favorite tour search engines. I always check both as their inventory varies depending on the destination.

4. Book Your Car

Use Discover Cars or to find the best car rental deals. I recommend comparing rental agency reviews on Google to ensure you are booking with the best company in that destination, as the reviews are often more accurate than the car rental search engines.

5. Don’t Forget Airport Lounge Access

Get a Priority Pass membership to gain access to 1,400+ VIP lounges and airport experiences worldwide. The Priority Pass app is the first thing I check when I have a layover. I’ve been a member for over a decade, and having a comfortable place to relax before and between flights makes air travel so much more enjoyable.

6. Don’t Forget Travel Insurance

I never leave the country without travel insurance. It provides comprehensive protection in case anything goes wrong (ie. illness, injury, theft, and cancelations, etc.). I use it frequently for my travels to stay protected.

My favorite companies that offer the best coverage and rates are:



  1. I live in Mykonos and I like to do various activities on the island that I recommend to those who want to visit it !! One of them is what you write and experience in your experiences, rent a boat in Mykonos and go to the beaches of Mykonos !! I will try this summer to do sailing and with your advice I think it will be a nice experience from island to island!

  2. My husband and i are doing a 10 day sail from Santorini in September. We will be traveling from Spain and then on to Italy. I’ve been told that G adventures doe not store your larger lugging and has no info to give me as to where might be the best place to do so. I find it hard to believe that I’m the first person who’s booked a sail tour that had larger luggage with them that needed to be stored while on their tour. Does anyone have ideas or suggestions for me please ? We are staying at the Kavalari hotel in Santorini the night before. I’ve tried to contact them from their web site to see if they will store my luggage and what the cost will be as i don’t want to spend my one night in Santorini trying to find a place that will do this but their website always gives me an error so I’ve been unable to email them.
    Any advice will be very appreciated. Thanks

Write A Comment